161344-84-9

Usage

Uses

Used in Chemical Synthesis:
2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is used as a dioxaborolane ligand for the preparation of enantiomerically enriched spiropentanes via zinc-catalyzed cyclopropanation of corresponding hydroxymethylallenes. This application is significant in the synthesis of complex organic molecules with specific stereochemistry, which is crucial for the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is used as a key intermediate in the synthesis of 1,2,3-trisubstituted cyclopropane derivatives. These derivatives are important building blocks for the development of various drugs, as they can be incorporated into the molecular structure of pharmaceutical compounds to enhance their biological activity and selectivity.
Used in Glycolipid Synthesis:
2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) is also used in the synthesis of glycolipids, specifically plakosides A and B, and their derivatives. This application is relevant in the field of natural product chemistry, as glycolipids are known to have various biological activities, including antimicrobial, antiviral, and anticancer properties. The synthesis of these complex molecules using the dioxaborolane ligand can lead to the development of novel therapeutic agents.
Overall, 2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLIC ACID BIS(DIMETHYLAMIDE) plays a vital role in the synthesis of various organic compounds, with applications spanning across the pharmaceutical, chemical, and natural product industries. Its unique chemical properties and versatility make it a valuable tool for researchers and chemists working on the development of new drugs, materials, and other specialty chemicals.

InChI:InChI=1/C12H23BN2O4/c1-6-7-8-13-18-9(11(16)14(2)3)10(19-13)12(17)15(4)5/h9-10H,6-8H2,1-5H3/t9-,10-/m0/s1

Upstream product

• 92527-13-4 [^(2-)-N,O,O'[2,2'-iminobis[ethanolato]]]-2-butylboron 
• 63126-52-3 (S,S)-(-)-2,3-dihydroxy-N,N,N',N'-tetramethylsuccinamide 
• 4426-47-5 butylboronic acid 

Downstream Products

• 89849-80-9 (1S,2R)-1-(tributylstannyl)-2-(hydroxymethyl)cyclopropane 
• 1192063-83-4 tert-butyl 4-{(1R,2S)-2-[(2R)-3-(benzyloxy)-2-hydroxy-propyl]cyclopropyl}piperidine-1-carboxylate 

Relevant academic research and scientific papers

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Callipeltosides A, B and C: Total Syntheses and Structural Confirmation

Since their isolation almost 20 years ago, the callipeltosides have been of long standing interest to the synthetic community owing to their unique structural features and inherent biological activity. Herein we present our full research effort that has led to the synthesis of these molecules. Key aspects of our final strategy include 1) synthesis of the C1-C9 pyran core (5) using an AuCl3-catalysed cyclisation; 2) formation of C10-C22 vinyl iodide (55) by sequential bidirectional Stille reactions and 3) diastereoselective union of these advanced fragments by means of an alkenylzinc addition (d.r.=91:9 at C9). The common callipeltoside aglycon (4) was completed in a further five steps. Following this, all three sugar fragments were appended to provide the entire callipeltoside family. In addition to this, D-configured callipeltose B was synthesised and appended to the callipeltoside aglycon. The 1H NMR spectrum of this molecule was found to be significantly different to the natural isolate, further supporting our assignment of callipeltoside B (2). Easy as A, B, C: The entire callipeltoside family of natural products have been synthesised in a highly convergent manner. This account details our full research effort and presents further evidence to aid in the stereochemical assignment of the glycosidic linkages present in callipeltosides B and C (see scheme).

CYCLOPROPYL AMINE DERIVATIVES

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compoun

Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications

A very effective chiral controller has been found for the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also been investigated with this system, but it was found that enantioenriched cyclopropylmethylamines are best prepared from enantioenriched cyclopropylmethanols.